Managing Director - AI Trainer - Freelance - 8-20 hrs/week - Remote

Updated: 27 April 2026

Are you a seasoned business leader passionate about shaping how AI understands and supports executive decision-making? Join us in advancing AI models’ ability to reason about high-level strategy, leadership, and operational excellence.

• Review and refine AI-generated content related to business strategy, organizational leadership, change management, and team building

• Evaluate AI outputs for realistic executive-level reasoning, business relevance, and adherence to best practices

• Develop real-world scenarios and case studies from your professional managing director experience

• Generate scenario variations from a variety of perspectives (e.g., managing director, board member, department head, or stakeholder)

• Identify and improve incomplete reasoning or gaps in AI content concerning leadership and management

In simple terms: You will evaluate and improve AI-generated executive content, ensuring it reflects authentic leadership strategies and operational processes. Rather than managing teams directly, you'll help AI models learn and reason like a real-world managing director.

• A senior-level managing director, CEO, or executive leader with significant professional experience in the EU or UK

• Deeply familiar with leading large organizations, defining business strategy, and overseeing complex operations

• Skilled at evaluating executive processes, team dynamics, and organizational health

• Comfortable working independently and delivering constructive feedback

• Available for 8–20 hours per week, with consistent communication